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Macrocyclization strategies for the total synthesis of cyclic depsipeptides
Organic & Biomolecular Chemistry, 2023Cyclic depsipeptides, bioactive natural products containing ester(s) and amides in the macrocycle, are synthesizedvia3 strategies, macrolactamization in solution, macrolactamization on-resin, and macrolactonization.
André R. Paquette, Christopher N. Boddy
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The Cyclic Depsipeptide Backbone of the Didemnins
Acta Crystallographica Section C Crystal Structure Communications, 1995An X-ray crystal analysis of phi-lactone N-¿1-¿N-¿4-¿[3- hydroxy-5-methyl-1-oxo-4-(N-L-threonylamino)heptyl]- oxy¿-2,5-dimethyl-1,3-dioxohexyl¿-L-leucyl¿-L-prolyl¿- N,O-dimethyl-L-tyrosine hydrobromide hydrate (1a), C42H66N5O11+.Br-.H2O, was obtained in order to determine the backbone folding of the macrocycle and to compare the results obtained with ...
S C, Mayer, P J, Carroll, M M, Joullié
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Cyclic depsipeptides as potential cancer therapeutics
Anti-Cancer Drugs, 2015Cyclic depsipeptides are polypeptides in which one or more amino acid is replaced by a hydroxy acid, resulting in the formation of at least one ester bond in the core ring structure. Many natural cyclic depsipeptides possessing intriguing structural and biological properties, including antitumor, antifungal, antiviral, antibacterial, anthelmintic, and ...
Jirouta, Kitagaki +4 more
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Total Synthesis of the Marine Cyclic Depsipeptide Viequeamide A
Journal of Natural Products, 2013The first total synthesis of viequeamide A, a natural cyclic depsipeptide isolated from a marine button cyanobacterium, was achieved with the N-Me-Val-Thr peptide bond as the final macrocyclization site. The synthetic product gave nearly identical spectroscopic data to that reported for the natural product.
Dongyu, Wang +5 more
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Total synthesis of aureobasidin a, an antifungal cyclic depsipeptide
Chemistry Letters, 1993Abstract A total synthesis of an antifungal cyclic depsipeptide aureobasidin A was first achieved mainly using PyBroP1) as a coupling reagent. The synthetic cyclized product was completely identical with the natural antibiotic in all respects. Some unexpected reactions due to N-methylamino acid were also described.
Toru Kurome +6 more
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Cyclic Depsipeptides, Callipeltins
2020Marine sponges are considered as an untapped reservoir of biologically active natural compounds exhibiting numerous interesting and potentially useful pharmacological activities, including antimicrobial, antifungal, cytotoxic, anti-inflammatory, and immunostimulatory activities.
Reda A. Abdelhamid, Hiroyuki Konno
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Synergistic action of a cyclic depsipeptide and piperazine on nematodes
Parasitology Research, 2000The present study describes the synergistic effects of the cyclic depsipeptide BAY 44-4400 and piperazine in the treatment against the nematodes Trichinella spiralis, Heligmosomoides polygyrus, and Heterakis spumosa. The in vitro anthelmintic activity of a combination of the two compounds (1.7 motility units) against T.
F, Nicolay +3 more
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Total synthesis of antimicrobial and antitumor cyclic depsipeptides
Chemical Communications, 2010The total synthesis of natural products "has to be viewed as an art and a science that needs to be advanced for its own sake" (K. C. Nicolaou) and indeed, the achievements within this field of chemistry during the last decades are astonishing. However, besides its inherent beauty, total synthesis also opens the gates widely to a better understanding of
Wenhua, Li +2 more
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Inhibition of Topoisomerase II by a Novel Antitumor Cyclic Depsipeptide, BE-22179 [PDF]
BE‐22179, a novel cyclic depsipeptide antibiotic having two 3‐hydroxyquinoline moieties, inhibited the DNA‐relaxing activity of L1210 topoisomerase II completely at 0.08 μM. This effect was far stronger than that of VP‐16. However, it did not show any marked effect on topoisomerase II‐mediated DNA cleavage.
Tomoko Yoshinari +2 more
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A Total Synthesis of the Cyclic Depsipeptide Chaiyaphumine‐A
ChemistrySelect, 2017Abstract The first total synthesis of Chaiyaphumine‐A, a cyclic depsipentapeptide isolated from Xenorhabdus SP. PB614 which showed good activity against Plasmodium falcifarum (IC 50 = 0.61 μM ...
Somnath S. Gholap, Sandip R. Ugale
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